When we visited his office on the Warner Bros. lot for this
year’s 100 Most Creative People in Business package, Conan O’Brien opened up
about how he works. He’s an analytical guy. He thinks a lot about the creative process, how to turn a
half-baked idea from a morning brainstorm into comedy gold (or a diamond–see below) by the
4:30 p.m. taping of his TBS late-night show.

In addition to our story, a running account of O’Brien putting
together a show last month, here he is talking at more length. For all the
preparation he does, the best material often comes from going off-script and reacting
in the moment. Which is like surfing. We’ll let him explain.

For audio from our Conan interview, click here. But these are his curated comments on creativity:

Creating a show is
like playing the horses.

Creativity
needs two ingredients, in comedy especially. It needs the sort of relaxing bull
shitting, left-brain throwing ideas around where 99 percent of it is a waste of
time. But then someone throws out a weird nugget or they’re just riffing on
something completely inconsequential and they come up with something great. And
then the next day is about we’re assembling them, we’re putting it together.
and you’ll see rehearsal is really key, because rehearsal is where everything
is put up… I can look at some things on paper and say it’s going to be great.
But you see it on its feet and you just know it’s not there. … That’s the thing
I can’t stress enough. In comedy, it’s a little bit akin to the, there’s the guy
that goes down to the racetrack, looks at the horses, talks to the jockey,
tastes the soil, measures the humidity. And he may do one percent better than
the kooky old lady who shows up and says, “I like the color blue and I’m going
to go for Blue Bottle in the fifth.”

No, wait–it’s
really like making of a jewel.

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It’s almost like when you make a diamond. You need
an incredible amount of pressure to turn carbon into a diamond, and I think as
you get closer and closer to the show, the pressure increases, and you start
running out of time and that’s when more and more key decisions are made.

Prepare like crazy so
you can wing it.

My formula has always been I’m big on preparing.
Prepare like crazy. But then just as you’re heading out, half an hour
beforehand, forget all of it. It’s there. It’s in your reptile brain. Go out but
feel loose enough to grab opportunities as they come up. Don’t just stick to
the plan if you see an opportunity. Now sometimes you go out there and the
energy is such that you just stick to the plan and you do fine. But when you
get out there and the energy is particularly good, I’m the first one to throw
out things left and right and just go for it. The show is always best when it’s
just play. When you’re playing, there’s a tension, yin-yang tension between
think beforehand and then just get out there, between preparation and
improvisation. And that’s been a lot of my career, finding the balance between
those two.

Improvising is like
surfing.

I’m very open to when things don’t work. That
becomes the fun. Obviously, Johnny Carson was really great at that. I’ve learned to really enjoy that. It’s surfing. You don’t know exactly how the wave is going to break. You get on it
and then you improvise. And I think there’s something, it’s really inspiring
actually, there’s something in the human mind that knows when something is
organic. That knows when something is happening in the moment. So the audience
will laugh at our prepared stuff but whenever things go off the rails and I
start shooting from the hip and then maybe going back and forth with Andy or a
guest, and we’re all shooting from the hip and we’re making it up as we go
along, the whole energy in the room changes. People know it. They know that
this is the real thing. They know that these cookies are being made fresh right
there in front of them. And it’s exciting.

Creativity should be
fun. Seriously.

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I used to be very intense at rehearsals. I just
found it wasn’t helping. So I’ve tried to learn and say let’s keep it light.
Let’s also not overcook things. Let’s try and get things into rough shape. One of
the qualities people like about what we’re doing is that it can feel very
loose. That’s the biggest comment I get from everybody on this new show: You look
like you’ve having so much fun. And the truth is you can’t fake it. You can
fake it a little bit, but you can’t fake it day after day.

Fostering a
collective comic sensibility is like cooking.

I do sympathize with how the batting average for
writing good material is really tough, so at the very least I’m trying to
create an atmosphere where failure is inevitable. And where everybody gets to
make fun of everybody. Do you know what I mean? I like to screw around with
them, try and make them laugh. One of my favorite things is to take out my iPhone
and be pretending to read them reviews of the show we just did which all praise
O’Brien’s ability to rise above the writing. And all these different ways of
insulting them. They know it’s all a joke…I used to think I need people to
marinate–this sounds disgusting–they need to marinate in the essence of
Conan. So I make sure that I’m around a lot. I’m just here. I’m roaming the
halls… So there’s this sense that they can pick up on how I think. Now we’ve
got so many people who have been with me for so long that some of them talk
like me. But then there’s also when someone comes up with something out of left
field that’s got a different energy and it’s good. It’s all of our excitement about
that that sends the message that it’s good to find those things.

What Conan has
learned from CEOs.

The last year has been completely improvised from
the time I sent out the [“People of Earth”] statement. And I think it’s been
one of my better years. I’m learning that not everything is in my control. I
heard once years ago, they did a study and they found that really successful
CEOs are good at knowing what’s in their control and what’s not in their
control… And I have learned that there are new cycles that good for a show like
mine. There are new cycles that bad for a show like mine. There are times when
the guests, great guests are coming left and right. There are times when you’re
really in a flow, things come and go, your opportunities come and go. It rains.
There’s a drought. It rains. The show is not all coming from me. My job here is
just to try and make the adjustments I can make, set a tone.

Conan’s pep talk to
the staff.

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My people tend to stick with me for a long time,
and I tend to stick with them. What I try to tell them especially with this new
show is, we’ve all been through a lot, we went through this tough time and made
it through to the other side. There’s a sense that it galvanized people here.
We stuck together. We kept our heads. We’re here, so let’s enjoy this. The
thing I keep telling them is the only way we can screw this up is by not being
bold enough. There is nothing to lose. Let’s just if we think of it, and we
think it’s funny let’s just try and make it happen.

About the author

Chuck Salter is a senior editor at Fast Company and a longtime award-winning feature writer for the magazine. In addition to his print, online and video stories, he performs live reported narratives at various conferences, and he edited the Fast Company anthologies Breakthrough Leadership, Hacking Hollywood, and #Unplug